Trisamino-s-triazines



United States Patent 3,410,855 TRISAMINO-s-TRIAZINES Denis Varsanyi, Arlesheim, and Willy Roth, Strengelbach, Switzerland, assignors to Geigy Chemical Corporation, Ardsley, N.Y., a corporation of New York No Drawing. Continuation-impart of applications Ser. No. 421,693, Dec. 28, 1964, and Ser. No. 560,855, June 27, 1966. This application June 12, 1967, Ser. No. 645,467 Claims priority, application Switzerland, Dec. 31, 1963, 16,070/63 18 Claims. ('Cl. 260-249.6)

ABSTRACT OF THE DISCLOSURE Trisamino-s-triazine derivatives in which one of the three amino groups is substituted by a radical QY in which Q is an alkylene or alkenylene radical and Y represents a hydrophilic substituent, which derivatives are useful as waxy components in surface treating agents.

This application is a continuation-in-part of our pending applications Ser. Nos. 421,693, filed Dec. 28, 1964, and 560,855, filed June 27, 1966, now abandoned, as a continuation-in-part of the former.

The present invention concerns new trisamino-s-triazine derivatives which are useful as waxy components in surface-treating agents.

By surface treating agents in the present description are meant agents which can ,be used for the protection and conservation, e.g. by coating or waxing, of surfaces of all types such as, for example, agents for the treatment of surfaces of inorganic materials, e.g. metal, stone, tiles, etc. and of organic materials, e.g. wood, leather, synthetic plastics such as linoleum, etc., textiles and paper.

More in particular, the surface treating agents containing novel trisamino-s-triazine according to the invention serve as floor polishes to render floors of all kinds of material smooth and glossy, while at the same time having an anti-slip effect. Floors to which the agents according to the invention have been applied, show a fine gloss, many of the novel s-triazine derivatives being selfpolishing, or the gloss of such treated floors and the like surfaces can be enhanced by subsequent rubbing with a soft cloth or the like well-known techniques. Floor polishes according to the invention can be applied to unsealed as well as to sealed floors.

However, the aforesaid surface-treating agents are not, themselves, wood-sealing agents; the latter are resinous compounds which close up the pores of floors made of wood or the like permanently or at least for a great length of time, e.g. for several years.

We have found that important components preferably in oil-based formulations of surface-treating agents are trisamino-s-triazine derivatives according to the invention which are of the general formula wherein:

R, R and R independently of each other represent hydro- 3,410,855 Patented Nov. 12, 1968 By cycloaliphatic radicals represented by R and R to R are meant monocyclic to tricyclic cycloalkyl and cycloalkenyl radicals, preferably of from 5 to 12 carbon atoms.

By optionally substituted aliphatic hydrocarbon radicals such as are represented by R, R to R in general Formula I are meant straight or branched chained alkyl or alkenyl radicals containing 122 carbon atoms, which radicals, for example, can be substituted by the hydroxyl group and/or one or more halogen atoms such as, e.g. fluorine or chlorine.

By hydrophilic substituents represented by Y in the general Formula I are meant, in particular, ionogenic hydrophilic substituents, both acid as well as basic groups, and also non-dissociating hydrophilic groups, such as, e.g. the following: the carboxyl, sulfonic acid, carbamyl, sulfamyl, monoor di-N-alkyl-sulfamyl, alkoxycarbonyl, hydroxyalkoxy-carbonyl, N-alkyl-carbarnyl, N-hydroxyalkyl-carbamyl, N-hydroxyalkyl, N-alkyl-carbamyl, N,N- di(hydroxyalkyl)-carbamyl, or an aminoalkoxy-carbonyl group, all above defined aliphatic radicals having at most 22, but preferably not more than 18 carbon atoms.

The alkylene or alkenylene radicals represented by Q in general Formula I preferably have straight chains and can contain l-2O carbon atoms.

The compounds of general Formula I are obtained by reacting, in any order desired, 2,4,6-trichloro-s-triazine with amines of the general Formulas II, III and IV:

R1 R R Na Na NI I R2 R4 QY (II) (II wherein R, R R R R Q and Y have the meanings given above. The reactions can be performed in the presence of a solvent which is inert to the reaction partners, a proton acceptor and an inert gas.

Preferably, the 2,4,6 trichloro-s-triazine (cyanuric chloride) is reacted first with an amine of the general Formula II or III at 0-5 C. (exothermic reaction), then with an amine or the general Formula III or II, respectively, at 4060 C., and finally with an amine of the general Formula IV at -175 C. The third chlorine atom is preferably substituted in the presence of a higher boiling aliphatic hydrocarbon, for instance, a petroleum fraction boiling at 170 C., as solvent.

The solvents usual for reactions of cyanuric chloride and amines such as water, chloroform, mixtures of acetone and water, and mixtures of other organic solvents and water, are used as solvents for the first and second steps.

The trisamino-s-triazine derivatives of the general Formula I wherein Y is an acid hydrophilic substituent which forms anions, can be isolated in the form of their metal and ammonium salts, preferably in the form of their alkali metal salts.

The compounds wherein Y is a functional carboxylic acid derivative can be produced by a variation of the process described above by reacting, in the known manner, a compound of general formula wherein R, R R R R and Q have the meanings given above and X is a halogen atom, a lower alkoxy radical, the phenoxy radical or the hydroxyl group, with an alkanolamine, dialkanolamine, alkenylenediamine or alkane diol.

Lower as used in this specification and in the appended claims in relation to an aliphatic radical, e.g. alkyl, means that such radical has at most 5 carbon atoms.

Preferred compounds due to their outstanding surfacefinishing properties are those of the following three classes:

(1) Compounds which in their free acid form are of wherein each of R, R and R represents a member selected from the group consisting of hydrogen, alkyl of from 1 to carbon atoms, cycloalkyl of from 6 to 12 ring carbon atoms, alkenyl of from 3 to 20 carbon atoms, hydroxyalkyl of from 2 to 20 carbon atoms, fiuoro-alkyl of from 3 to 20 carbon atoms, and chloro-alkyl of from 3 to 20 carbon atoms,

R represents a member selected from the group consisting of alkyl of from 1 to 22 carbon atoms, cycloalkyl of from 5 to 12 and preferably 6 to 12 ring carbon atoms, alkenyl of from 3 to 22 and preferably 3 to 20 carbon atoms, hydroxy-alkyl of from 2 to 22, and preferably 3 to 20 carbon atoms, fiuoro-alkyl of from 3 to 22 and preferably 3 to 20 carbon atoms, and chloroalkyl of from 3 to 22 and preferably 3 to 20 carbon atoms,

R represents a lipophilic radical, preferably as defined under R in this formula,

Q represents a member selected from the group consisting of alkylene of from 1 to 20 carbon atoms and alkenylene of from 3 to 20 carbon atoms, and, in this class, Y is Y representing a member selected from the group consisting of -COOH and SO H,

and in which compounds the total number of carbon atoms in R R R and R taken together is preferably at least 12 and most preferably the total number of carbon atoms of the last-named four substituents together with the number of carbon atoms in QY is at least 17;

and which substances surpass those of the following classes of this invention in their capacity of imparting a fine gloss to surfaces of the type described to which they have been applied.

(I I) Compounds which in their free acid form are of the same formula as those of class (I), but wherein Y is replaced by Y which latter represents a member selected from the group consisting of carbamyl, sulfamyl, monoand di-alkyl-substituted carbamyl and su-lfamyl wherein alkyl has from 1 to 16 carbon atoms, and N-hydroxyalkyl-substituted carbamyl and sulfamyl wherein alkyl is of from 2 to 6 carbon atoms;

(III) Compounds which in their free acid form are of the same formula as those of class (I), but wherein Y is replaced by Y which latter represents a member selected from the group consisting of alkoxy carbonyl of from 2 to 18 carbon atoms, hydroxy-alkoxy carbamyl of from 2 to 18 carbon atoms and amino-alkoxy-carbonyl, mono-(lower alkyl)amino-alkoxycarbonyl and di-lower alkyl)amino-alkoxy-carbonyl, the alkoxy portion in the last three members having from 2 to 6 carbon atoms.

The trisamino-s-triazine derivatives of the general Formula I have wax-like properties; they are generally handwaxes, of a hardness of about 1 to 5 as determined by the ASTM penetration method; they are resistant to chemicals, especially to alkalis and acids, and especially to household chemicals; they can be used instead of natural waxes or together therewith for the treatment and finishing of such surfaces as, for example, agents for the treatment of surfaces of inorganic materials, e.g. metal surfaces such as chromed metal parts, polished stone, ceramic tiles, but also as gloss-imparting and surface-protecting agents for automobile bodies of organic materials, e.g. wood, leather, plastic resinous material such as linoelum, etc., on textiles as hydrophilic agents and paper as carriers for copying layers. They have characteristic properties also possessed by natural waxes such as solubility in lipophilic solvents, are compatible with natural and synthetic waxes, can be converted readily to pastes and have good gelling properties, e.g. with organic solvents, particularly with low boiling petroleum fractions, and have a good solvent retaining power. Surfaces treated therewith can be given a high gloss upon light polishing.

The metal and ammonium salts, the addition salts of inorganic and organic acids and the quaternary ammonium salts of the compounds of general Formula I can have similar properties and can be used instead of or together with natural waxes for the above-described purposes.

Surface finishing agents according to the invention are obtained by mixing a trisamino-s-triazine derivative of the general Formula I or several such, derivatives with the usual substances which are sutiable for the treatment of surfaces. Such substances are, for example, the following: natural and synthetic waxes, resins, silicones, etc., which improve the physical properties, also solvents, as well as inorganic and organic fillers, e.g. silicates, milled plastics, anionic, cationic or non-ionic dispersing agents, cleansing agents such as, e.g. natural and synthetic soaps, tensioactive substances, pigments, agents to improve the stability to light, stabilizers of all types such as corrosion inhibitors, scents, dyestuffs, biocidal active substances or agents containing such substances, e.g. insecticides, fungicides, bactericides, etc.

The content of compounds of Formula I in such agents ranges from 0.2 to about 50%, of the total weight of the agent.

The surface finishing agents containing compounds of the invention can be in the form of and used as aerosols, solvents, emulsions, semi-solid and solid pastes. The agents can thus serve to protect and to finish surfaces of all types, by which is also included the treatment of paper, e.g. the production of carbon paper.

The following non-limitative examples illustrate the invention further. Parts and percentages are given therein by weight and the temperatures are in degrees centigrade.

EXAMPLE 1 370 parts of cyanuricchloride (technically pure) are dissolved by slightly heating in 3000 parts by volume of carbon tetrachloride in a sulphonating flask and the solution is then cooled to 0-3". 1078 parts of n-octadecylamine (technically pure) in finely pulverised form are then added in portions within about 3 hours while stirring and cooling intensively. Cooling is necessary because the reaction is strongly exothermic. A solution of 220 parts of sodium carbonate (technically pure, dry), dissolved in 1000 parts by volume of distilled water is then added slowly dropwise within about 40 minutes while cooling well. The reaction mixture is brought to room temperature while stirring and then slowly brought to the boil whereupon it is refluxed for 4-5 hours. The resultant product is cooled to room temperature while stirring, and the solid part is filtered otf under suction and washed three times on the filter with 300 parts by volume of carbon tetrachloride.

The filter residue is crushed and dried in about 24 hours in a vacuum dryer at 5060/14200 torr. The reaction product is slurried twice with about 6000 parts by volume of warm distilled water and the water is removed. 2-chlorotions in about 30-40 minutes at 0-5 while intensively stirring and cooling. Good cooling is necessary as the reaction is strongly exothermic. A solution of 55 parts of sodium carbonate (technically pure, dry), dissolved in 200 parts by volume of distilled water is then added slowly dropwise within 30 minutes while cooling well. Here again, the reaction is exothermic so that good cooling is necessary. The whole reaction mixture is thereupon stirred for 3 hours at this temperature. After the cooling bath has been removed, 101 parts of ll-amino-undecylic acid (technically pure) are added in portions in about 30-40 minutes while stirring vigorously. The inner temperature during this addition is 10-15". A solution of 27 parts of sodium carbonate (technically pure, dry), in

4,6-bis-n-octadecylamino-s-triazine is obtained as a snow 100 parts by volume of distilled water is then added dropwhite powder. It melts at 139-140 and the yield is 86% wise at this temperature within about 15-20 minutes. The of the theoretical. whole reaction mixture is then brought to the boil and 42 parts of ll-amino-undecane carboxylic acid (techrefluxed for another 5 hours. It is then cooled to room nically pure) are then suspended in 500 parts by volume of temperature while stirring and mixed, in the flask, with gasoline and the suspension is heated to 70-80. parts 20 1500 parts by volume of acetone. It is filtered under sucof sodium hydroxide (technically pure), freshly pulvertion, the crude product is dried in a vacuum dryer at ised, are then added in small portions within 5-10 minunder 14-20 torr pressure and the organic solvent is utes while stirring intensively and the whole is stirred for removed. The reaction product is then stirred twice with another 11 /2 hours at a temperature of -80". 130 about 5000 parts by volume of warm distilled water and Parts of finely pulverised 2 chloro-4,6-bis-n-octadecyl- 25 filtered off under suction. The reaction product is dried in amino-s-triazine are then added in portions within about a vacuum dryer at 50-60 under 14-20 torr pressure. 30-40 minutes while stirring vigorously. The mixture is 11 [2 chloro 4' n octadecylamino s triazinyl then stirred under reflux under an atmosphere of nitrogen, (6') ]-amino-undecylic acid, in the form of the sodium for 2 hours at a temperature of -100", then for 2 hours salt, is obtained as a snow white powder. The yield is at a temperature of 130-140 and finally for 18 hours at 30 about of the theoretical and it melts at 138-140 C. a temperature of 160-170". The contents of the flask are 60.4 parts Of 11-[2'chl0r0-4'-n-octadecylamino-s-trithen cooled to while stirring and the solid part is azinyl-(6)]-amino-undecylic acid sodium salt and 52.2 filtered off on a steam filter upon which there is a 3-4 parts of di-n-octadecylamine are dissolved at 70-80 in mm. thick layer of the kieselguhr Hyflo-Super-Cel 500 parts by volume of gasoline, and 5 parts of finely pul which has been slurried with a little gasoline. The residue 35 verized sodium hydroxide are added to this solution. The is washed twice with 100 parts by volume of hot solvent temperature of the reaction mixture is brought to each time. The solution obtained, which is barely opaleswithin about 4 hours while introducing nitrogen and cent, is evaporated to dryness in a rotary evaporator and the reaction mixture is stirred for about 18 hours at this the residue is dried in a vacuum dryer at 60-70 under temperature. After cooling to 100, the reaction mixture about 14-20 mm. ressure. Th sodium alt f 11-[2,4- 40 is filtered hot with the aid of Hyflo-Super Cel and then bis n octadecylamino-s-triazinyl-(6)]-amino-undecylic the solvent is distilled off from the filtrate. As residue, acid is obtained in a yield of about 98% of the theoretical the P Sodium Salt of Y as a pale yellowish product which melts at 188-190". yl min S ri i yl amino undecylic acid is obtained in a yield of about 98% of the theoretical. Example 2 45 It melts at 98-100. Compounds falling under Formula I in which R, -Q In a sulphonatrng flask, 95 parts of cyanunc chloride Y R R R d R4 are the groups given in the f ll i (technlcally P am dissolved y gently heating in 1500 table, are obtained by the procedure of Examples 1 and parts by volume of carbon tetrachloride and the solution 2, respectively, but using correspondingly substituted is then cooled to 0-3. 135 parts of finely pulverized n- 50 starting materials in equivalent amounts in view of the octadecylamine (technically pure) are then added in pormaterials used in the said examples.

TABLE R QY R1 R2 R3 R4 3.. II -C oHgoCOONfl H ll-CrgHgn I'I n-C 3II 7 4 H -C1|JH20CO0N2] H Il-Cr H 1 H-C13IH37 n-CwHzn 5".-. CH3 C5H10CO0H 03H! C3117 01:13 C12Hg5 s Allyl Oleyl 00 OH CH CH C3111 can fi-hydroxyethyl C H COONa H 011151 H 0 ,11 8.-- CFg-(CH;z)z- CsHmCOONa ll Cal-[ 7 l1 Il-C131'I37 9....-- CHzCl. C5H10C 00H C2115 C2115 II (115K133 (kHz-CH 10. H Olcyl-COONa Allyl CH3 Allyl C1BH31 H CwHzoSOaH II Allyl II 01511131 12 H C HHSO H HOCHzCHz/ Ho-CH CH2- H Oleyl. 13"-- CEHB CiuHgoSOgH CzHg CgH5 HO-CHz C zI'Iz5 (EH 14. H C H QOOOK CI CHT CIIE CI'IZ Cl-OH -OH om o l-I 15..-- H CH -SO H H EXAMPLE 100 (liquid floor Wax) (oil based) 5.25 parts of the sodium salt of 1l-[2,4-bis-n-octadecyl amino-s-triazinyl- 6) ]-amino-undecylic acid,

0.75 part of vinyloctadecyl ether polymerisate (M.P.

1.50 parts of microcrystalline petroleum wax (M.P. 74-

76 C.; penetration ASTM 7.50 parts of paraflin (M.P. 5052 C.),

5.00 parts of 1,4-dioxan,

80.00 parts of petroleum fraction (boiling range 150- The components are mixed with each other by heating at 120 C. and the resulting clear solution is quickly cooled while stirring, whereupon a homogeneous gel-like liquid is formed. This is used as liquid floor wax on wood or linoleum floors to give a very good gloss.

EXAMPLE 101 (aerosol floor wax) (oil-based) The components which are solid or liquid at normal temperature are mixed with each other with heating at C. and the resulting solution is quickly cooled while stirring. The mixture formed is placed in a pressure container fitted with a spray valve and propellant gas is added. The mixture formed, which can be sprayed, is excellently suitable as floor wax. It gives a good gloss on wooden floors and has excellent shelf-like.

EXAMPLE 102 (furniture polish) (oil-water emulsion type) 1.25 parts of 11-[2',4'-bis-n-didodecylamino-s-triazinyl- (6)]-amino-undecylic acid,

5.00 parts of dimethylpolysiloxane (viscosity 300 c.p.s./

1.25 parts of sorbitan monolaurate,

1.25 parts of polyoxyethylene sorbitan monolaurate,

43.75 parts of petroleum fraction (boiling range 47.50 parts of water.

The organic components are mixed with each other by heating at 100 C. and the boiling water is added to this hot solution while stirring vigorously. The mixture is cooled while stirring whereupon a homogeneous, white liquid is formed which is excellently suitable for the care of furniture.

EXAMPLE 103 (water-repellant aerosol for use on textiles) (oil-based) 5.00 parts of 11-[2'-n-octadecylamino-4'-di-n-octadecylannino-s-triazinyl-(6')]-amino-undecylic acid, 15.00 parts of perchloroethylene,

40.00 parts of trichlorofiuoromethane, 40.00 parts of dichlorodifluoromethane.

11-[2'-n-octadecylamino 4' di-n-octadecylamino-striazinyl-(G')]-amino-undecylic acid is dissolved in the perchloroethylene. This solution is placed in a pressure container fitted with a spray valve and the propellant gases (trichlorofluoromethane and dichlorodifluoromethane)are added. The sprayable mixture formed is excellently suitable for attaining a water repellent effect on textiles such as cotton, particularly when the invisible coating formed is ironed.

EXAMPLE 104 (car polish) (oil water emulsion type) The organic components which are solid and liquid at normal temperature are dissolved at 100 C. and the boiling water is added to this hot solution while stirring vigorously. The mixture is cooled while stirring and then placed in a pressure container fitted with a spray valve and the propellant gases (propane and butane) are added. The sprayable mixture so formed is excellently suitable for application on exterior surfaces of automobile body parts and other laquered metal surface. The mixture is rubbed on lightly and thereby imparts to such surfaces a high gloss.

EXAMPLE 105 (carbon paper) 42.00 parts of 11-[2-n-octadecylamino 4' octadecene- (8 -ylamino-triazinyl- 6) ]-amino-undecylic acid,

5.00 parts of petroleum jelly,

26.00 parts of spindle oil,

.00 parts of anhydrous lanolin,

1.2 parts of the base of Victoria Blue B,

0.6 part of methyl violet,

2.2 parts of olein,

6.00 parts of milori blue,

12.00 parts of carbon black.

Carbon black, milori blue and spindle oil are finely milled in a color triple roll mill. The remaining components are added to this mixture and the whole is heated to 120 C. while stirring until a homogeneous preparation is formed. A thin layer of this mixture is evenly applied by means of a heatable calender to one side of a carbon-supporting paper. Thereby, carbon paper is obtained which is suitable for the production of copies.

We claim:

1. A compound selected from among (a) a melamine derivative of the formula wherein each of R, R and R represents a member selected from among: hydrogen, alkyl of from 1 to 20 carbon atoms, cycloalkyl of from 6 to 12 ring carbon atoms, alkenyl of from 3 to 20 carbon atoms, hydroxy-alkyl of from 2 to 20 carbon atoms, fluoroalkyl of from 3 to 20 carbon atoms, and chloroalkyl of from 3 to 20 carbon atoms,

and each of R and R represents a member selected from among: alkyl of from 1 to 20 carbon atoms, cycloalkyl of from 6 to 12 ring carbon atoms, alkenyl of from 3 to 20 carbon atoms, hydroxy-alkyl of from 2 to 20 carbon atoms, fiuoro-alkyl of from 3 to 20 carbon atoms, and chloro-alkyl of from 3 to 20 carbon atoms,

Q represents a member selected from among alkylene of from 1 to 20 carbon atoms and alkenylene of from 3 to 20 carbon atoms, and

Y represents a member selected from COOH, SO H, carbamyl, sulfamyl, the latter two members substituted at the nitrogen atom thereof by one or two substituents selected from alkyl of from 1 to 16 carbon atoms and hydroxyalkyl of from 2 to 6 carbon atoms, alkoxycarbonyl of from 2 to 18 carbon atoms, hydroxy-alkyoxy-carbonyl of from 2 to 18 carbon atoms and amino-alkoxy-carbonyl wherein alkoxy has from 2 to 6 carbon atoms and wherein the amino nitrogen is unsubstituted or substituted by one or two lower alkyl, and

(b) an alkali metal or ammonium or acid-addition salt thereof.

2. A compound as defined in claim 1, wherein Y is --COOH.

3. A compound as defined in claim 1, wherein Y is -SO H.

4. A compound as defined in claim 1, wherein Y is selected from carbamyl, sulfamyl and each of these tWo members is substituted at the nitrogen atom thereof by one or two substituents selected from alkyl of from 1 to 16 carbon atoms and hydroxy-alkyl of from 2 to 6 carbon atoms.

5. A compound as defined in claim 1, wherein Y is selected from alkoXy-carbonyl of from 2 to 18 carbon atoms, hydroxy-alkoxy-carbonyl of from 2 to 18 carbon atoms and amino-alkoxy-carbonyl wherein alkoxy has from 2 to 6 carbon atoms and wherein the amino nitrogen atom is substituted by one or two lower alkyl.

6. A compound as defined in claim 1, wherein the total number of carbon atoms of R R R and R taken together is at least 12.

7. A compound as defined in claim 1, wherein the total number of carbon atoms of R R R R and -QY taken together is at least 17.

8. A compound as defined in claim 1, which is 2-[2',4'- bis-n-octadecylamino-s-triazinyl-(6')-amino] acetic acid or a salt thereof with a base.

9. A compound as defined in claim 1, which is 6-[2,4 bis-n-octadecylamino-s-triazinyl-(6')-amino]-caproic acid or a salt thereof with a base.

10. A compound as defined in claim 9, which is the sodium salt of 6-[2',4-bis-n-octadecylamino-s-triazinyl- (6)-amino]-caproic acid.

11. A compound as defined in claim 1, which is 11-[2', 4'-bis-n-octadecylamino-s-triazinyl (6) amino] undecylic acid or a salt thereof with a base.

12. A compound as defined in claim 11, which is the sodium salt of 11-[2',4'-bis-n-octadecylamintrs-triazinyl- (6)-amino]undecy1ic acid.

13. A compound as defined in claim 11, which is the potassium salt of 11-[2,4'-bis-n-octadecylamino-s-triazinyl-(6)-amino]-undecylic acid.

14. A compound as defined in claim 1, which is 11- [2,4'-bis-n-octadec 8" en ylamino s triazinyl-(6')- amino]-undecylic acid or a salt thereof with a base.

13 14 15. A compound as defined in claim 1, which is 11-[2'- R represents a lipophilic radical selected from the group n-octadecylamin-4' di-n octadecylamino s triazinylconsisting of alkyl of from 10 to 18 carbon atoms and (6)]-amino-undecylic acid or a salt thereof with a base. alkenyl of from 10 to 18 carbon atoms,

16. A compound which in its free acid form is of the Q represents a member selected from the group consistformula ing of alkylene of from 1 to 20 carbon atoms and al- R kenylene of from 3 to 20 carbon atoms, Y represents a member selected from the group consist- N ing of carbamyl, sulfamyl, monoand di-alkyl-substi- QY1 tuted carbamyl and sulfamyl wherein alkyl has from 1 to 16 carbon atoms, and N-hydroxy-alkyl-substituted R1 N N R3 carbamyl and sulfamyl wherein alkyl is of from 2 to 6 L L carbon atoms. \N 18. A compound of the formula wherein each of R, R and R represents a member selected from the group consisting of hydrogen, alkyl of from 1 to i Q,Y3 carbon atoms, cyclo-alkyl of from 6 to 12 ring carbon atoms, alkenyl of from 3 to 20 carbon atoms, hydroxy- R1 N N Ra alkyl of from 2 to 20 carbon atoms, fluoro-alkyl of 20 L from 3 to 20 carbon atoms, and chloro-alkyl of from N 3 to 20 carbon atoms, R3 R4 R represents a member selected from the group consistwherein each of ing of alkyl of from 1 to 20 carbon atoms, cycloalkyl of from 6 to 12 ring carbon atoms, alkenyl of from 3 to 20 carbon atoms, hydroxy-alkyl of from 2 to 20 carbon atoms, fluoro-alkyl of from 3 to 20 carbon atoms, and chloro-alkyl of from 3 to 20 carbon atoms,

R represents a lipophilic radical selected from the group consisting of alkyl of from 10 to 18 carbon atoms and alkenyl of from 10 to 18 carbon atoms,

Q represents a member selected from the group consisting of alkylene of from 1 to 20 carbon atoms and alkylene of from 3 to 20 carbon atoms, and

Y represents a member selected from the group consist- R, R and R represents a member selected from the group consisting of hydrogen, alkyl of from 1 to 20 carbon atoms, cycloalkyl of from 6 to 12 ring carbon atoms, alkenyl of from 3 to 20 carbon atoms, hydroXy-alkyl of from 2 to 20 carbon atoms, fluoro-alkyl of from 3 to 20 carbon atoms, and chloro-alkyl of from 3 to 20 carbon atoms,

R represents a member selected from the group consisting of alkyl of from 1 to 20 carbon atoms, cycloalkyl of from 6 to 12 ring carbon atoms, alkenyl of from 3 to 20 carbon atoms, hydroxy-alkyl of from 2 to 20 carbon atoms, fluoro-alkyl of from 3 to 20 carbon atoms, mg of COOH and SO3H' and chloro-alkyl of from 3 to 20 carbon atoms, 17. A compound of the formula R represents a lipophilic radical selected from the group R consisting of alkyl of from 10 to 18 carbon atoms and alkenyl of from 10 to 18 carbon atoms, Q represents a member selected from the group consisti Q. 2 ing of alkylene of from 1 to 20 carbon atoms and alkenylene of from 3 to 20 carbon atoms, and R1 N N Rs Y represents a member selected from the group consisti ing of alkoxy-carbonyl of from 2 to 18 carbon atoms, N hydroXy-a1koxy-carbonyl of from 2 to 18 carbon atoms R2 and amino, mono-alkyl-aminoand di-alkyl-amino-alwherein each of koxy-carbonyl wherein alkoxy has from 2 to 6 carbon R, R and R represents a member selected from the group atomsconsisting of hydrogen, alkyl of from 1 to 20 carbon atoms, cycloalkyl of from 6 to 12 ring carbon atoms, References Cited alkenyl of from 3 to 20 carbon atoms, hydroxy-alkyl of UNITED STATES PATENTS from 2 to 20 carbon atoms, fluoro-alkyl of from 3 to 2 909 421 10/1959 Gysin et a1 260 249 6 ig ff g g f and of 3 3,143,548 8/1964 Vail et al 260--249.6 R2 represents a member selected from the group consistegxg i izf i ing of alkyl of from 1 to 20 carbon atoms, cycloalkyl of from 6 to 12 ring carbon atoms, alkenyl of from 3 to 20 carbon atoms, hydroxy-alkyl of from 2 to 20 carbon HENRY JILES "nary Exammer' atoms, fluoro-alkyl of from 3 to 20 carbon atoms, and J. M. FORD, Assistant Examiner. chloro-alkyl of from 3 to 20 carbon atoms, 

